Yup. Especially Annapolis area, but surrounding too. Pretty much all stores in downtown (clothing and all) allow dogs inside. All restaurants have outdoor patio seating where they're allowed. All the local Lowe's, Home Depot's, etc are all pet friendly, as far as I know, they've never questioned me. Lots of pet stores, boutiques, grooming places, parks, etc. Banks all give out doggy biscuits. He's been with me to a few different car places - car wash allows him in while I pay, then we go sit outside and wait for my car to be done, mechanics let him inside while they rotate my tires, change oil, etc. I think maybe because we're by lots of water - we have a lot of outdoor restaurants, lots of people bring their dogs on their boat, etc.
MD actually made a 'law' about it not too long ago..
http://www.wusa9.com/news/local/story.aspx?storyid=156846